Playboy Advisor: Dildos, Threesomes and the Five-Inch Swallow

By Playboy Advisor

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Playboy Advisor: Dildos, Threesomes and the Five-Inch Swallow:

Having recently gone through a rough breakup, I dusted off the movie Forgetting Sarah Marshall, a gem on the topic. In one scene the main character, Peter, is out on the town, looking for some rebound action. He says to two women, “I just came out of a five-year relationship, so I’m not looking for anything serious, just sexual activity.” As a newly single guy with nothing to lose, I can’t help but fantasize about being able to pull off such a brazen stunt. Not to be greedy, but I think I could actually pull it off with two women. A ménage à trois would go a long way toward healing my broken heart. Do you think I can make blunt work?

—R.M., Paso Robles, CaliforniaWe don’t recommend blunt. It makes for good comedy in movies, but in reality it’s brutish, offensive and virtually guaranteed to make a woman feel like little more than a piece of meat. Direct can work, but be earnest, complimentary and specific about what you find attractive about the woman you’re interested in. You’re complicating matters by bringing up a threesome, a fantasy that sits statistically low on the scale of awesome shit people wish happened more often. We’ve found a ménage à trois becomes an achievable scenario when the green light is glaringly obvious: Are the two women gazing longingly at you, whispering to each other and then gazing longingly at you again? In that case, go for it. But rare is the random ménage between strangers that doesn’t involve a three-day EDM festival and copious molly. An informal poll of successful ménage a trotskies revealed that it’s most likely to happen between friends or at least acquaintances who have had time to establish mutual trust. But that doesn’t prevent post-ménage complications: A couple who hooked up with a good female friend consider the ménage the beginning of the end of their relationship. The boyfriend came in his girlfriend’s best friend. The two women didn’t trust each other afterward, and the girlfriend never trusted her boyfriend again. One friend of ours managed a ménage à quatre with three women, which devolved into an air-traffic-control nightmare with nobody ever landing. Be careful what you wish for, but if you pull it off, please let us know.

Years ago, when we were dating and experimental, my now wife and I bought a harness and dildo for her to wear. I found it the other day when I was cleaning out my closet, and I’m wondering how to propose to my wife that we finally take off the hangtag and put it to good use 10 years after buying it.

—D.D., Miami Beach, Florida

Do it as romantically and playfully as possible on your wedding anniversary. Present the dildo to her bundled with a dozen roses and a picture of the two of you during your courtship. Follow that with dinner at an old haunt, where you can reminisce over those early days of oxytocin-fueled euphoria. We assume the unused dildo was more a totem of trust than a tool for intimacy and pleasure—and that if you didn’t need it then, you probably won’t need it later that night. But it doesn’t hurt to try, provided you use plenty of lube.

How do women in porn movies swallow a nine- or 10-inch cock all the way to the hilt with seeming ease when giving head? My wife can barely handle my puny five inches without gagging.

—D.G., Concord, California

Expecting your wife to be able to perform like an adult-film star is asking a lot of her. Porn is adult entertainment, not adult education. Just as most movie action heroes aren’t able to execute a perfect flying kick on the first take, adult-film performers don’t always deep throat flawlessly. Like any actor, they need to prepare for their roles. Provided your wife isn’t trying to tell you something with her gagging, here are a few tricks of the trade you can share with her: She can practice relaxing her throat by inserting two fingers into the back of her mouth until her gag reflex subsides over time. She can fold her left thumb into her palm and clench a fist, an anti-gagging trick that dentists recommend to patients in the chair. Or she can use a numbing agent such as Comfortably Numb Deep Throat spray. Bonus blow job fact: The reason porn actors look up into a man’s eyes while fellating him is to keep their eyes from tearing up.

For answers to reasonable questions relating to food and drink, fashion and taste, sex and dating, write the Playboy Advisor, 9346 Civic Center Drive, Beverly Hills, California 90210, or e-mail advisor@playboy.com.


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